Synthesis of stable and potent δ/μ opioid peptides: Analogues of H-Tyr-c[D-Cys-Gly-Phe-D-Cys]-OH by ring-closing metathesis

Journal of Medicinal Chemistry

Volumn 50, Issue 13, 2007, Pages 3138-3142

  Mollica, Adriano ^a   Guardiani, Giovanni ^b   Davis, Peg ^c   Ma, Shou Wu ^c   Porreca, Frank ^c   Lai, Josephine ^c   Mannina, Luisa ^e,f   Sobolev, Anatoli P ^f   Hruby, Victor J ^d  

^a UNIVERSITY OF CHIETI   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

^c UNIVERSITY OF ARIZONA COLLEGE OF MEDICINE   (United States)

^d University of Arizona   (United States)

^e UNIVERSITY OF MOLISE   (Italy)

^f CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; DELTA OPIATE RECEPTOR; ENKEPHALIN DERIVATIVE; ENKEPHALIN[2,5 DEXTRO ALLYLGLYCINE]; HYDROXYTYROSINE[DEXTRO CYSTEINYLGLYCYLPHENYLALANYL DEXTRO CYSTEINE]AMINE; KAPPA OPIATE RECEPTOR; LIGAND; MU OPIATE RECEPTOR; REDUCED BOND ENKEPHALIN[2,5 DEXTRO ALLYLGLYCINE]; TRITIUM; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CATALYSIS; CATALYST; DISULFIDE BOND; DRUG POTENCY; DRUG SELECTIVITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GUINEA PIG; HYDROGENATION; MOUSE; NONHUMAN; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ANALYSIS; VAS DEFERENS;

ALLYL COMPOUNDS; ANIMALS; ENKEPHALINS; GUINEA PIGS; ILEUM; MALE; MICE; MICE, INBRED ICR; MUSCLE CONTRACTION; MUSCLE, SMOOTH; MYENTERIC PLEXUS; PEPTIDES, CYCLIC; RADIOLIGAND ASSAY; RECEPTORS, OPIOID, DELTA; RECEPTORS, OPIOID, KAPPA; RECEPTORS, OPIOID, MU; STRUCTURE-ACTIVITY RELATIONSHIP; VAS DEFERENS;

EID: 34347270982     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm061048b     Document Type: Article

References (48)

1. Li, P.; Roller, P. P. Cyclization strategies in peptide derived drug design. Curr. Top. Med. Chem. 2002, 2, 325-341.
2. Hruby, V. J. Conformational restrictions of biologically active peptides via amino acid side chain groups. Life Sci. 1982, 31, 189-199.
3. Creighton, T.E. Proteins: Structures and Molecular Properties; W.H. Freeman and Company: New York, 1993.
4. (a) Schiller, P. H.; DiMaio, J.; Nguyen, T. M. D. Activity profiles of conformationally restricted opioid peptide analogs. Proc. FEBS Congr. 16th 1985, B, 457-462.
5. (b) Froimowitz, M.; Hruby, V. J. Conformational analysis of enkephalin analogs containing a disulfide bond. Models for delta- and mu-receptor opioid agonists. Int. J. Pept. Prot. Res. 1989, 34, 88-96.
6. (c) Hruby, V.J.; Gehrig, C. A. Recent developments in the design of receptor specific opioid peptides. Med. Res. Rev. 1989, 9, 343-401.
7. 5]enkephalinamide, conformationally constrained cycle enkephalinamide analogues with delta receptor specificity. Biochem. Biophys. Res. Commun. 1982, 106, 506-512.
8. (a) Mosberg, H. I.; Hurst, R.; Hruby, V. J.; Cree, K.; Yamamura, H. I.; Galligan, J. J.; Burks, T. F. Bis Penicillamine enkephalins possess highly improved specificity toward δ opioid receptors. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 5871-5871.
9. 3]DPDPE. J. Am. Chem. Soc. 1996, 118, 2143-2152.
10. (c) Bartosz-Bechowski, H.; Davis, P.; Zalewska, T.; Slaninova, J.; Porreca, F.; Yamamura, H. I.; Hruby, V. J. Cyclic enkephalin analogs with exceptional potency at peripheral δ opioid receptors. J. Med. Chem. 1994, 37, 146-150.
11. 5]enkephalin in acqueous solution determined by NMR and energy minimization calculations. J. Am. Chem. Soc. 1988, 110, 3351-3359.
12. 5]enkephalin binding to δ opiate receptors in the rat brain and neuroblastoma-glioma hybrid cell line (NG 108-15). Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 2543-2547.
13. (a) Voyer, N.; Lamothe, J. The use of peptidic frameworks for the construction of molecular receptors and devices. Tetrahedron 1995, 51, 9241-9284.
14. (b) Kaul, R.; Balaram, P. Stereochemical control of peptide folding. Bioorg. Med. Chem. 1999, 7, 105-117.
15. (c) Andrews, M. J. I.; Tabor, A. B. Forming stable helical peptides using natural and artificial amino acids. Tetrahedron 1999, 55, 11711-11743.
16. (c) Hruby, V. J.; Al-Obeidi, F.; Kasmierski, W. M. Emerging approaches in the molecular design of receptor selective peptide ligands: conformational topographical and dynamic considerations. Biochem. J. 1990, 268, 249-262.
17. (a) DiMaio, J.; Schiller, P. W. A cyclic enkephalin analog with high in vitro opiate activity. Proc. Nat. Acad. Sci. U.S.A. 1980, 77, 7162-7166.
18. (b) DiMaio, J.; Nguyen, T. M. D.; Lemieux, C.; Schiller, P. W. Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogs: Effect of conformational constraints on opiate receptor selectivity. J. Med. Chem. 1982, 25, 1432-1438.
19. (c) Schiller, P. W.; Nguyen, T. M. D.; Miller, J. Synthesis of side-chain to side-chain cyclized peptide analogs on solid supports. Int. J. Pept. Prot. Res. 1985, 25, 171-177.
20. (d) Siemion, I. Z.; Szewczuk, Z.; Herman, Z. S.; Stachura, Z. To the problem of biologically active conformation of enkephalin. Mol. Cell. Biochem. 1981, 34, 23-29.
21. Keller, O.; Rudinger, J. Synthesis of (1,6-alpha,alpha′- diaminosuberic acid)oxytocin ("dicarba-oxytocin"). Helv. Chim. Acta 1974, 57, 1253-1259.
22. Stymiest, J. L.; Mitchell, B. F.; Wong, S.; Vederas, J. C. Synthesis of biologically active dicarba analogues of the peptide hormone oxytocin using ring-closing metathesis. Org. Lett. 2003, 5, 47-49.
23. (a) Grubbs, R. H.; Chang, S. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 1998, 54, 4413-4450.
24. (b) Armstrong, S. K. Ring closing diene metathesis in organic synthesis. J. Chem. Soc, Perkin Trans. I 1998, 371-388.
25. (c) Blackwell, H. E.; Grubbs, R. H. Highly efficient synthesis of covalently cross-linked peptide helices by ring closing metathesis. Angew. Chem., Int. Ed. 1998, 37, 3281-3284.
26. (a) Celanire, S.; Descamps-Francois, C.; Lesur, B.; Guillaumet, G.; Joseph, B. Synthesis of 14-membered ring jaspamide derivatives. Lett. Org. Chem. 2005, 2, 528-531.
27. (b) Wels, B.; Kruijtzer, J. A. W.; Garner, K.; Nijenhuis, W. A. J.; Gispen, W. H.; Adan, R. A. H.; Liskamp, R. M. J. Synthesis of a novel potent cyclic peptide MC4-ligand by ring-closing metathesis. Bioorg. Med. Chem. 2005, 13, 4221-4227.
28. (c) Stymiest, J. L.; Mitchell, B. F.; Wong, S.; Vederas, J. C. Synthesis of oxytocin analogues with replacement of sulfur by carbon gives potent antagonists with increased stability. J. Org. Chem. 2003, 70, 7799-7809.
29. (d) Schmidt, B.; Kuhn, C.; Ehlert, D. K.; Lindeberg, G.; Lindman, S.; Karlen, A.; Hallberg, A. A frame shifted disulfide bridged analogue of angiotensin II. Bioorg. Med. Chem. 2003, 11, 985-990.
30. α-tetrasubstituted α-amino acids. Chemo-enzymatic synthesis and application to turn-forming peptides. Tetrahedron 2001, 57, 6567-6577.
31. (a) Schiller, P. W.; Weltrowska, G.; Berezowska, I.; Lemieux, C.; Chung, N. N.; Wilkes, B. C. Synthesis and in vitro opioid activity profiles of novel cyclic enkephalin analogs. In Understanding Biology Using Peptides; Proceedings of the 19th American Peptide Symposium, June 18-23, San Diego CA, 2005; Blondelle, S. E., Ed.; American Peptide Society: La Costa, CA, 2005.
32. (b) Schiller, P. W. Opioid peptide analog design: from cyclic enkephalins to orally active analgesics. Biopolymers 2005, 80, 492.
33. (a) Han, So.-Y.; Kim, Y. A. Recent development of peptide coupling reagents in organic synthesis. Tetrahedron 2004, 60, 2447.
34. (b) Kim, Y.-A.; Han, So.-Y. Comparative study of cyanuric fluoride and Bop-Cl as carboxyl activators in peptide coupling reactions. Bull. Korean Chem. Soc. 2000, 21, 943-946.
35. (a) Trnka, T. M.; Grubbs, R. H. The development of L2X2Ru:CHR olefin metathesis catalysts: An organometallic success story. Acc. Chem. Res. 2001, 34, 18-29.
36. (b) Chatterjee, A. K.; Grubbs, R. H. Synthesis of trisubstituted alkenes via olefin cross-metathesis. Org. Lett. 1999, 11, 1751-1753.
37. (c) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands. Org. Lett. 1999, 6, 953-956.
38. (a) Kessler, H.; Seip, S. NMR of Peptide. In Two-dimensional NMR Spectroscopy: Application for Chemists and Biochemists, 2nd ed.; Croasmun, W. R., Carlson, R. M. K., Eds.; VCH Publishers: New York, 1994; pp 619-650.
39. (b) Braun, S.; Kalinowski, H. O.; Berger S. 150 and More Basic NMR Experiments, 2nd ed.; Wiley-VCH: Weinheim, 1998.
40. Kramer T. H.; Davis P.; Hruby V. J.; Burks T. F.; Porreca F. In vitro potency, affinity and agonist efficacy of highly selective delta opioid receptor ligands J. Pharmacol. Exp. Ther. 1993, 266, 577-584.
41. Wang, Z.; Gardell, L. R.; Ossipov, M. H.; Vanderah, T. W.; Brennan, B. B.; Hochgeschwender, U.; Hruby, V. J.; Malan, T. P., Jr.; Lai, J.; Porreca, F. Pronociceptive actions of dynorphin maintain chronic neuropathic pain. J. Neurosci. 2001, 21, 1779-1786.
42. 35S]thio)triphosphate to NG108-15 cell membranes: Characterization of agonist and inverse agonist effects. J. Pharm. Exp. Ther. 1997, 283, 1284-1284.
43. (a) Misicka, A.; Lipkowski, A. W.; Horvath, R.; Davis, P.; Kramer, T. H.; Yamamura, H. I.; Hruby, V. J. Topographical requirements for delta opioid ligands: Common structural features of dermenkephalin and deltorphin. Life Sci. 1992, 51, 1025-1032.
44. (b) Hosohata, K.; Varga, E. V.; Alfaro-Lopez, J.; Tang, X.; Vanderah, T. W.; Porreca, F.; Hruby, V. J.; Roeske, W. R.; Yamamura, H. I.; (2S,3R)β-methyl-2′,6′-dimethyltyrosine- L-tetrahydroisoquinoline-3-carboxylic acid [(2S,3R)TMT- L-Tic-OH] is a potent, selective δ opioid receptor antagonist in mouse brain. J. Pharmacol. Exp. Ther. 2003, 304, 683-688.
45. 5]enkephalin. J. Med. Chem. 1991, 34, 1823-1830.
46. 5]-enkephalin with δ opioid receptor selectivity. J. Med. Chem. 1992, 35, 2384-2391.
47. (a) Ananthan, S. Opioid ligands with mixed μ/δ opioid receptor interactions: An emerging approach to novel analgesics. AAPS PharmSciTech 2006, 8, 118-125 and references cited therein.
48. (b) Horan, P. J.; Mattia, A.; Bilsky, E. J.; Weber, S.; Davis, T. P.; Yamamura, H. I.; Malatynska, E.; Appleyard, S. M.; Slaninova, J.; Misicka, A.; Lipkowski, A. W.; Hruby, V. J.; Porreca, F. Antinociceptive profile of biphalin, a dimeric enkephalin analog. J. Pharmacol. Exp. Ther. 1993, 265, 1446-54.